clavulanic acid

CHEBI:48947 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

Antibiotic isolated from Streptomyces clavuligerus. It acts as a suicide inhibitor of bacterial β-lactamase enzymes. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:64509

Chemical structure

Computed structure properties
Molecular formula	C8H9NO5
Charge	0
Average mass	199.162 Da
Monoisotopic mass	199.04807 Da
Source	ChEBI
InChIKey	HZZVJAQRINQKSD-PBFISZAISA-N

SMILES

[H][C@@]12CC(=O)N1[C@@H](C(=O)O)/C(=C/CO)O2

InChI

InChI=1S/C8H9NO5/c10-2-1-4-7(8(12)13)9-5(11)3-6(9)14-4/h1,6-7,10H,2-3H2,(H,12,13)/b4-1-/t6-,7-/m1/s1

Also called

acide clavulanique (INN)— chebi
acidum clavulanicum (INN)— chebi
ácido clavulánico (INN)— chebi
(2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
(2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-OXO-4-OXA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID (EXACT_SYNONYM)— chebi
(Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
Clavulanate (EXACT_SYNONYM)— chebi
Clavulanic acid (EXACT_SYNONYM)— chebi
Clavulansäure (EXACT_SYNONYM)— chebi
MM 14151 (EXACT_SYNONYM)— chebi
antibiotic MM 14151 (EXACT_SYNONYM)— chebi
clavulonic acid (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antibacterial drug CHEBI:36047

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:48947`	clavulanic acid	`antibioticmech:chebi-e6f3165a79`	2026-08-30

Producer organisms

Organisms that biosynthesize this compound. Cluster link evidence is how the upstream source graded the gene cluster, so it is populated only for a source that grades it. An empty cell is not weaker support: a curator-authored producer carries its support in Evidence instead. Where the source entry named several compounds, the evidence is marked inherited, meaning it covers this compound together with the cluster's other products rather than singling it out. Those products need not be related to each other: a cluster can list an intermediate, a precursor and a finished antibiotic side by side.

Producer organisms
Organism	BGC	Cluster link evidence	Source	Quality	Note	Evidence
Streptomyces clavuligerus NCBITaxon:1901 strain ATCC 27064	BGC0000845	Enzymatic assays; Heterologous expression compound specific	MIBIG 4.0.1 (entry 5)	questionable	MIBiG active entry; compound 'clavulanic acid' joined by exact Standard InChIKey.	PMID:8088547 (MIBiG's first legacy reference for the entry, inherited rather than attached to the compound. It supports that the entry exists; it is NOT established as evidence for this specific producer/compound link.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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